{
 "cells": [
  {
   "cell_type": "code",
   "execution_count": 1,
   "id": "figured-representation",
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "3.13.2 | packaged by conda-forge | (main, Feb 17 2025, 14:10:22) [GCC 13.3.0]\n",
      "2025.09.1\n"
     ]
    }
   ],
   "source": [
    "import sys\n",
    "import pandas as pd\n",
    "import numpy as np\n",
    "from rdkit import rdBase, Chem, DataStructs\n",
    "from rdkit.Chem import AllChem, Draw, Descriptors, PandasTools, rdMolDescriptors\n",
    "from rdkit.Chem import EnumerateStereoisomers\n",
    "PandasTools.RenderImagesInAllDataFrames(True)\n",
    "from rdkit.Chem.Draw import IPythonConsole\n",
    "from rdkit.Chem.Draw import rdDepictor\n",
    "\n",
    "rdDepictor.SetPreferCoordGen(True)\n",
    "IPythonConsole.molSize = (350,300)\n",
    "IPythonConsole.ipython_useSVG=True\n",
    "IPythonConsole.drawOptions.addStereoAnnotation = True\n",
    "\n",
    "print(sys.version)\n",
    "print(rdBase.rdkitVersion)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 2,
   "id": "double-tender",
   "metadata": {},
   "outputs": [
    {
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       "</svg>"
      ],
      "text/plain": [
       "<IPython.core.display.SVG object>"
      ]
     },
     "execution_count": 2,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "m = Chem.MolFromSmiles('NC(C)C(=O)O')\n",
    "m_ccw = Chem.MolFromSmiles('N[C@H](C)C(=O)O')\n",
    "m_cw = Chem.MolFromSmiles('N[C@@H](C)C(=O)O')\n",
    "m_unk = Chem.MolFromSmiles('N[C@@H](C)C(=O)O |w:1.1|')\n",
    "Chem.ReapplyMolBlockWedging(m_unk)\n",
    "Draw.MolsToGridImage([m,m_ccw,m_cw,m_unk],legends=['','R','S','unknown'],molsPerRow=4)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 3,
   "id": "adjustable-berkeley",
   "metadata": {},
   "outputs": [
    {
     "data": {
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      "text/plain": [
       "<IPython.core.display.SVG object>"
      ]
     },
     "execution_count": 3,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "m_ccw_abs = Chem.MolFromSmiles('N[C@H](C)C(=O)O |a:1|')\n",
    "m_and = Chem.MolFromSmiles('N[C@H](C)C(=O)O |&1:1|')\n",
    "m_or = Chem.MolFromSmiles('N[C@H](C)C(=O)O |o1:1|')\n",
    "Draw.MolsToGridImage([m_ccw_abs,m_and,m_or],legends=['R', 'R and S','R or S'])"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 4,
   "id": "naughty-covering",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "</svg>"
      ],
      "text/plain": [
       "<IPython.core.display.SVG object>"
      ]
     },
     "execution_count": 4,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "m_and = Chem.MolFromSmiles('N[C@H](C)C(=O)O |&1:1|')\n",
    "m_and_1 = Chem.MolFromSmiles('N[C@H](C)C(=O)O |a:1|')\n",
    "m_and_2 = Chem.MolFromSmiles('N[C@@H](C)C(=O)O |a:1|')\n",
    "Draw.MolsToGridImage([m_and,m_and_1,m_and_2])"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 5,
   "id": "charged-bandwidth",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "</svg>"
      ],
      "text/plain": [
       "<IPython.core.display.SVG object>"
      ]
     },
     "execution_count": 5,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "m2_cis = Chem.MolFromSmiles('O[C@H]1CC[C@H]1N |&1:1,4|')\n",
    "m2_cis_1 = Chem.MolFromSmiles('O[C@H]1CC[C@H]1N |a:1,4|')\n",
    "m2_cis_2 = Chem.MolFromSmiles('O[C@@H]1CC[C@@H]1N |a:1,4|')\n",
    "\n",
    "m2_trans = Chem.MolFromSmiles('O[C@H]1CC[C@@H]1N |&1:1,4|')\n",
    "m2_trans_1 = Chem.MolFromSmiles('O[C@H]1CC[C@@H]1N |a:1,4|')\n",
    "m2_trans_2 = Chem.MolFromSmiles('O[C@@H]1CC[C@H]1N |a:1,4|')\n",
    "\n",
    "Draw.MolsToGridImage([m2_cis,m2_cis_1,m2_cis_2,m2_trans,m2_trans_1,m2_trans_2],legends=['\"cis\"','','','\"trans\"','',''],molsPerRow=3)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 6,
   "id": "occasional-missile",
   "metadata": {
    "scrolled": true
   },
   "outputs": [
    {
     "data": {
      "image/png": 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       "' fill='#000000'/>\n",
       "<path class='CIP_Code' d='M 233.7 115.4\n",
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       "L 229.9 123.4\n",
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       "' fill='#000000'/>\n",
       "</svg>\n"
      ],
      "text/plain": [
       "<rdkit.Chem.rdchem.Mol at 0x7efe280b8510>"
      ]
     },
     "execution_count": 6,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "m = Chem.MolFromSmiles('OC[C@H]1OC=C[C@@H](O)[C@@H]1O') # CHEMBL2115567\n",
    "m"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 7,
   "id": "palestinian-lodge",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "image/png": 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       "</svg>\n"
      ],
      "text/plain": [
       "<rdkit.Chem.rdchem.Mol at 0x7efe280b9460>"
      ]
     },
     "execution_count": 7,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "three_centers = Chem.MolFromSmiles('OC[C@H]1OC=C[C@@H](O)[C@@H]1O |&1:2,o2:6,8|') \n",
    "three_centers"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 8,
   "id": "changing-stations",
   "metadata": {},
   "outputs": [
    {
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       "<path class=\"CIP_Code\" d=\"M 333.5 80.2 Q 333.5 81.6, 333.1 82.8 Q 332.7 83.9, 331.9 85.2 L 331.4 84.8 Q 332.0 83.6, 332.3 82.6 Q 332.6 81.5, 332.6 80.2 Q 332.6 78.9, 332.3 77.9 Q 332.0 76.8, 331.4 75.6 L 331.9 75.3 Q 332.7 76.5, 333.1 77.7 Q 333.5 78.8, 333.5 80.2 \" fill=\"#000000\"/>\n",
       "</svg>"
      ],
      "text/plain": [
       "<IPython.core.display.SVG object>"
      ]
     },
     "execution_count": 8,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "mix1_1 = Chem.MolFromSmiles('OC[C@H]1OC=C[C@@H](O)[C@@H]1O') \n",
    "mix1_2 = Chem.MolFromSmiles('OC[C@@H]1OC=C[C@@H](O)[C@@H]1O') \n",
    "Draw.MolsToGridImage([mix1_1,mix1_2])"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 9,
   "id": "silver-problem",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "<path class=\"CIP_Code\" d=\"M 333.6 80.2 Q 333.6 81.6, 333.2 82.8 Q 332.8 83.9, 332.0 85.2 L 331.4 84.8 Q 332.1 83.6, 332.4 82.6 Q 332.7 81.5, 332.7 80.2 Q 332.7 78.9, 332.4 77.9 Q 332.1 76.8, 331.4 75.6 L 332.0 75.3 Q 332.8 76.5, 333.2 77.7 Q 333.6 78.8, 333.6 80.2 \" fill=\"#000000\"/>\n",
       "</svg>"
      ],
      "text/plain": [
       "<IPython.core.display.SVG object>"
      ]
     },
     "execution_count": 9,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "mix2_1 = Chem.MolFromSmiles('OC[C@H]1OC=C[C@H](O)[C@H]1O') \n",
    "mix2_2 = Chem.MolFromSmiles('OC[C@@H]1OC=C[C@H](O)[C@H]1O') \n",
    "Draw.MolsToGridImage([mix2_1,mix2_2])"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 10,
   "id": "golden-departure",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "</svg>"
      ],
      "text/plain": [
       "<IPython.core.display.SVG object>"
      ]
     },
     "execution_count": 10,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "opts = EnumerateStereoisomers.StereoEnumerationOptions()\n",
    "opts.onlyStereoGroups = True\n",
    "enumerated = EnumerateStereoisomers.EnumerateStereoisomers(three_centers)\n",
    "Draw.MolsToGridImage(list(enumerated))"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 11,
   "id": "false-presence",
   "metadata": {},
   "outputs": [
    {
     "data": {
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       "<path class=\"bond-8 atom-8 atom-9\" d=\"M 390.4,333.7 L 395.8,333.7\" style=\"fill:none;fill-rule:evenodd;stroke:#FF0000;stroke-width:1.0px;stroke-linecap:butt;stroke-linejoin:miter;stroke-opacity:1\"/>\n",
       "<path class=\"bond-8 atom-8 atom-9\" d=\"M 390.1,330.1 L 396.1,330.1\" style=\"fill:none;fill-rule:evenodd;stroke:#FF0000;stroke-width:1.0px;stroke-linecap:butt;stroke-linejoin:miter;stroke-opacity:1\"/>\n",
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       "<path class=\"stereoGroup\" d=\"M 402.4 350.1 Q 402.4 348.6, 403.2 347.8 Q 404.0 346.9, 405.4 346.9 Q 406.8 346.9, 407.6 347.8 Q 408.4 348.6, 408.4 350.1 Q 408.4 351.7, 407.6 352.5 Q 406.8 353.4, 405.4 353.4 Q 404.0 353.4, 403.2 352.5 Q 402.4 351.7, 402.4 350.1 M 403.6 350.1 Q 403.6 351.3, 404.0 351.9 Q 404.5 352.5, 405.4 352.5 Q 406.3 352.5, 406.7 351.9 Q 407.2 351.3, 407.2 350.1 Q 407.2 349.0, 406.7 348.4 Q 406.3 347.8, 405.4 347.8 Q 404.5 347.8, 404.0 348.4 Q 403.6 349.0, 403.6 350.1 \" fill=\"#000000\"/>\n",
       "<path class=\"stereoGroup\" d=\"M 410.3 347.0 L 410.5 347.9 Q 411.1 346.9, 412.2 346.9 Q 412.5 346.9, 413.0 347.0 L 412.8 348.0 Q 412.3 347.9, 412.0 347.9 Q 411.5 347.9, 411.2 348.1 Q 410.8 348.3, 410.6 348.8 L 410.6 353.3 L 409.4 353.3 L 409.4 347.0 L 410.3 347.0 \" fill=\"#000000\"/>\n",
       "<path class=\"stereoGroup\" d=\"M 414.2 352.3 L 416.0 352.3 L 416.0 345.9 L 414.0 346.5 L 413.7 345.8 L 416.3 344.6 L 417.2 344.7 L 417.2 352.3 L 418.9 352.3 L 418.9 353.3 L 414.2 353.3 L 414.2 352.3 \" fill=\"#000000\"/>\n",
       "</svg>"
      ],
      "text/plain": [
       "<IPython.core.display.SVG object>"
      ]
     },
     "execution_count": 11,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "m1 = Chem.MolFromSmiles('OC[C@H]1OC=C[C@@H](O)[C@@H]1O |&1:2,o2:6,8|') \n",
    "m2 = Chem.MolFromSmiles('OC[C@@H]1OC=C[C@@H](O)[C@@H]1O |&1:2,o2:6,8|') \n",
    "m3 = Chem.MolFromSmiles('OC[C@H]1OC=C[C@H](O)[C@H]1O |&1:2,o2:6,8|') \n",
    "m4 = Chem.MolFromSmiles('OC[C@@H]1OC=C[C@H](O)[C@H]1O |&1:2,o2:6,8|') \n",
    "\n",
    "Draw.MolsToGridImage([m1,m2,m3,m4],molsPerRow=2,subImgSize=(250,250))"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 12,
   "id": "juvenile-silence",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "image/png": "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       "<path class='CIP_Code' d='M 223.2 155.3\n",
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       "' fill='#000000'/>\n",
       "</svg>\n"
      ],
      "text/plain": [
       "<rdkit.Chem.rdchem.Mol at 0x7efe2828a730>"
      ]
     },
     "execution_count": 12,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "m = Chem.MolFromSmiles('OC[C@H]1OC=C[C@@H](O)[C@@H]1O') # CHEMBL2115567\n",
    "IPythonConsole.drawOptions.addAtomIndices = True\n",
    "m"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 13,
   "id": "effective-cotton",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "image/png": 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       "' fill='#000000'/>\n",
       "<path class='stereoGroup' d='M 211.7 162.3\n",
       "L 214.3 162.3\n",
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       "L 214.7 151.5\n",
       "L 215.9 151.7\n",
       "L 215.9 162.3\n",
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       "' fill='#000000'/>\n",
       "</svg>\n"
      ],
      "text/plain": [
       "<rdkit.Chem.rdchem.RWMol at 0x7efe28336200>"
      ]
     },
     "execution_count": 13,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "sgmol = Chem.RWMol(m)\n",
    "sg = Chem.CreateStereoGroup(Chem.StereoGroupType.STEREO_AND, sgmol, [6,8])\n",
    "sgmol.SetStereoGroups([sg])\n",
    "sgmol"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 14,
   "id": "adverse-playback",
   "metadata": {},
   "outputs": [
    {
     "data": {
      "image/png": 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       "</svg>\n"
      ],
      "text/plain": [
       "<rdkit.Chem.rdchem.RWMol at 0x7efe280914e0>"
      ]
     },
     "execution_count": 14,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "IPythonConsole.drawOptions.addAtomIndices = False\n",
    "\n",
    "sgmol = Chem.RWMol(m)\n",
    "sg = Chem.CreateStereoGroup(Chem.StereoGroupType.STEREO_AND, sgmol, [6,8])\n",
    "sgmol.SetStereoGroups([sg])\n",
    "sgmol"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "id": "amazing-savings",
   "metadata": {},
   "outputs": [],
   "source": []
  }
 ],
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